EP2576526A1 - Dérivés d'alcanol thiosubstitués hétérocycliques utilisés comme fongicides - Google Patents

Dérivés d'alcanol thiosubstitués hétérocycliques utilisés comme fongicides

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Publication number
EP2576526A1
EP2576526A1 EP11721049.2A EP11721049A EP2576526A1 EP 2576526 A1 EP2576526 A1 EP 2576526A1 EP 11721049 A EP11721049 A EP 11721049A EP 2576526 A1 EP2576526 A1 EP 2576526A1
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EP
European Patent Office
Prior art keywords
plants
alkyl
formula
species
plant
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP11721049.2A
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German (de)
English (en)
Inventor
Carl Friedrich Nising
Pierre Cristau
Jörg Nico GREUL
Hendrik Helmke
Gorka Peris
Tomoki Tsuchiya
Pierre Wasnaire
Peter Dahmen
Jürgen BENTING
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Intellectual Property GmbH
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Bayer Intellectual Property GmbH
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Filing date
Publication date
Application filed by Bayer Intellectual Property GmbH filed Critical Bayer Intellectual Property GmbH
Priority to EP11721049.2A priority Critical patent/EP2576526A1/fr
Publication of EP2576526A1 publication Critical patent/EP2576526A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/24—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel heterocyclic thio-substituted alkanol derivatives, to processes for preparing these compounds, to compositions containing these compounds and to their use as biologically active compounds, in particular for controlling harmful microorganisms in plant protection and in the protection of materials and as plant growth regulators.
  • X stands for 0 or S
  • Y stands for S, SO or S0 2 ,
  • n 0 or 1
  • n 0 or 1
  • R is in each case optionally substituted alkyl, alkenyl, cycloalkyl or aryl,
  • R 1 is hydrogen, SH, alkylthio, alkoxy, halogen, haloalkyl, haloalkylthio, haloalkoxy,
  • A represents optionally substituted aryl and optionally substituted heteroaryl, and their agrochemically active salts.
  • the salts thus obtainable also have fungicidal and / or plant growth regulatory properties.
  • heterocyclic thio-substituted alkanol derivatives which can be used according to the invention are generally defined by the formula (I).
  • Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) and to all intermediates (see also below under “Explanatory Notes on Processes and Intermediates”). is preferably for S.
  • Y is preferably S or SO 2 .
  • Y particularly preferably represents S.
  • m is preferably 0.
  • n is preferably 0.
  • n is also preferably 1.
  • R preferably represents in each case optionally branched C3-C 7 alkyl, Ci-Cg haloalkyl, C 2 -C 7 alkenyl, C 2 -C 7 haloalkenyl, optionally substituted by halogen, Ci-C i-alkyl, Ci- C 1 -haloalkyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 1 -C 4 -haloalkylthio or C 1 -C 4 -alkylthio-substituted C 3 -C 7 -cycloalkyl and also, where appropriate, monosubstituted to trisubstituted by halogen or C 1 -C 4 Alkyl substituted phenyl.
  • R particularly preferably represents in each case optionally branched C3-C5 alkyl, Ci-C ö haloalkyl, C3-C5 alkenyl, C3-C5 haloalkenyl, optionally substituted by halogen, Ci-C4-alkyl, C1 -C4- haloalkyl, Ci-C4-haloalkoxy, Ci-C4-alkoxy, Ci-C4-haloalkylthio or Ci-C4-alkylthio, substituted C 3 -C 6 cycloalkyl.
  • R particularly preferably represents tert-butyl, isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl, 1-methylthiocyclopropyl, 1-trifluoromethylcyclopropyl, (3-one) -4-chloro-2-methylbut- 3-en-2-yl, C 1 -C 4 -haloalkyl.
  • R 1 is preferably hydrogen, SH, C 1 -C 4 -alkylthio, C 1 -C 4 -alkoxy or halogen.
  • R 1 particularly preferably represents hydrogen, SH, methylthio, ethylthio, methoxy, ethoxy, fluorine, chlorine, bromine or iodine.
  • A is preferably unsubstituted or mono- to trisubstituted by Z 1 phenyl, wherein
  • A is also preferably in each case optionally mono- or polysubstituted by Z 2 substituted five- or six-membered heteroaryl selected from furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, triazolyl, tetrazolyl, oxadiazolyl, thiadiazolyl, pyridinyl , Pyridazinyl, pyrimidinyl, pyrazinyl and triazinyl, wherein
  • Z 2 represents halogen, Ci-C4-alkyl, Ci-C 4 alkylthio, dC 4 alkoxy, Ci-C 4 haloalkyl, C r C 4 - Halogenthioalkyl, Ci-C4-haloalkoxy, C3-C 7 - Cycloalkyl, in each case optionally substituted by halogen or Ci-C 4 alkyl substituted phenyl, phenoxy or phenylthio.
  • A is also particularly preferably each optionally mono- or polysubstituted by Z 2 substituted five- or six-membered heteroaryl selected from 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1- Pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1-pyrazolyl, 1H-imidazol-2-yl, 1H-imidazol-4-yl, 1H-imidazol-5-yl, 1H-imidazol-1-yl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, lH-l, 2,3-triazol-1-yl,
  • Z 2 represents halogen, Ci-C4-alkyl, Ci-C2 alkylthio, dC 2 alkoxy, Ci-C 2 haloalkyl, C r C 2 - Halogenthioalkyl, Ci-C2 haloalkoxy, C3-C6-cycloalkyl , is in each case optionally monosubstituted by halogen or Ci-C i-alkyl phenyl or phenoxy.
  • A is also very particularly preferably in each case optionally mono- or polysubstituted by Z 2 substituted five- or six-membered heteroaryl selected from 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl , 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3 -Isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1H-1,2,3-triazol-1-yl, 1H-1,2,3-triazol-4-yl , 1H-l, 2,3-triazol-5-y
  • Z 2 is fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-, i-, s- or t-butyl, cyclopropyl, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trichloromethyl, difluoromethyl, difluoro- ormethoxy, difluoromethylthio, dichloromethyl, difluorochloromethyl, difluorochloromethoxy.
  • Halogen (also in combinations such as haloalkyl, haloalkoxy, etc.) fluorine, chlorine, bromine and iodine;
  • Alkyl (also in combinations such as alkylthio, alkoxy, etc.) saturated, straight-chain or branched hydrocarbon radicals having 1 to 8 carbon atoms, for example Ci-C6-alkyl such as methyl, ethyl, propyl, 1-methyl ethyl, butyl, 1-methylpropyl, 2 Methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl , 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-di
  • Haloalkyl (also in combinations such as haloalkylthio, haloalkoxy, etc.) straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above, for example Ci-C3 Haloalkyl such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl,
  • Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and a double bond in any position, e.g.
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propeny
  • Cycloalkyl monocyclic saturated hydrocarbon groups having 3 to 8 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • Aryl unsubstituted or substituted, aromatic, mono-, bi- or tricyclic ring, e.g. Phenyl, naphthyl, anthracenyl (anthryl), phenanthracenyl (phenanthryl).
  • Hetaryl unsubstituted or substituted, unsaturated heterocyclic 5- to 7-membered ring containing up to 4 nitrogen atoms or alternatively 1 nitrogen atom and up to 2 further heteroatoms selected from N, O and S: eg 2-furyl, 3-furyl, 2 Thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 1-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 1-pyrazolyl, 1H-imidazol-2-yl, 1H-imidazole-4 yl, 1H-imidazol-5-yl, 1H-imidazol-1-yl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazol-yl, 3-isothiazolyl, 4-isothiazo
  • heterocyclic thio-substituted alkanol derivatives of the formula (I) can be prepared in various ways (cf., EP-A 0 409 418). In the following, the possible methods are first shown schematically. Unless indicated otherwise, the radicals given have the meanings given above.
  • M 2 stands for a metal, eg lithium.
  • R la is chlorine and Si (alkyl) 3 .
  • R lb is hydrogen, chlorine and Si (alkyl) 3 .
  • Y 1 stands for S.
  • R lc is SH, alkylthio, alkoxy, halogen, haloalkyl, haloalkylthio, haloalkoxy, cyano,
  • Y 1 stands for S.
  • Y 2 stands for SO or S0 2 .
  • ketones of the formula (III) which are furthermore required as starting materials of process A according to the invention are known (cf., EP-A 0 409 418).
  • the process A according to the invention is usually carried out in the presence of a diluent, e.g. Diethyl ether, tetrahydrofuran or dichloromethane, carried out at temperatures of -80 ° C to + 80 ° C.
  • a diluent e.g. Diethyl ether, tetrahydrofuran or dichloromethane
  • the resulting product is trapped with a proton donor.
  • the reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • the (Het) aryl (thio) methyl ketones of the formula (IV) required as starting materials in carrying out the process B according to the invention are known in some cases. They can be prepared in a known manner (cf EP-A 0 409 418).
  • organometallic heterocycles of the formula (V) which are furthermore required as starting materials of process B according to the invention are known (cf., EP-A 0 409 418 and EP-A 0 395 175).
  • organometallic heterocycles of formula (V) it may be advantageous to provide the 2-position with a suitable protecting group, for example trimethylsilyl, to direct M 2 to the 5-position.
  • a suitable protecting group for example trimethylsilyl
  • This protecting group may, but need not, be cleaved prior to reaction with the ketones of formula (IV).
  • the process B according to the invention is usually carried out in the presence of a diluent, for example tetrahydrofuran or diethyl ether, at temperatures of -120 ° C. to + 80 ° C.
  • a diluent for example tetrahydrofuran or diethyl ether
  • the reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • R a is in each case optionally substituted alkyl (with the exception of tert-butyl, when X is S), alkenyl, cycloalkyl or aryl.
  • R a preferably represents in each case optionally branched C3-C7- alkyl (except for tert-butyl, if X is S), Ci-Cg haloalkyl, C2-C7 alkenyl, C2-C 7 haloalkenyl, optionally C 3 -C 7 -cycloalkyl which is substituted by halogen, C 1 -C -alkyl, C 1 -C -haloalkyl, C 1 -C -alkoxy, C 1 -C -haloalkoxy, C 1 -C 4 -haloalkylthio or C 1 -C 4 -alkylthio and optionally phenyl monosubstituted to trisubstituted by halogen or C 1 -C 4 -alkyl.
  • R a particularly preferably represents in each case optionally branched C3-C5 alkyl except tert-butyl, Ci-C ö haloalkyl, C3-C5 alkenyl, C3-C5 haloalkenyl, optionally substituted by halogen, Ci-C 4 -Alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio or C 1 -C 4 -alkylthio-substituted C 3 -C 6 -cycloalkyl.
  • R a is very particularly preferably isopropyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, 1-methylcyclopropyl, 1-methoxycyclopropyl, 1-methylthiocyclopropyl, (3 lb) -4-chloro-2-methylbut-3-ene-2 yl, C 1 - C 4 haloalkyl.
  • New oxirane derivatives of the formula (VIII-a) are also the subject of this invention.
  • the process C according to the invention is carried out in the presence of a diluent, e.g. N, N-dimethylformamide, and optionally in the presence of a base, e.g. Sodium hydride or potassium carbonate.
  • a diluent e.g. N, N-dimethylformamide
  • a base e.g. Sodium hydride or potassium carbonate.
  • oxirane derivatives of the formula (IX) required as starting materials for carrying out the process D according to the invention are known in some cases (cf., EP-A 0 121 171).
  • 2-Chloro-l, 3-thiazole of the formula (X) is known.
  • organometallic compounds in particular alkyllithium compounds (for example n-butyllithium) (cf EP-A 0 395 175).
  • the process D according to the invention is usually carried out in the presence of a diluent, e.g. Tetrahydrofuran or diethyl ether, carried out at temperatures of -120 ° C to + 80 ° C.
  • a diluent e.g. Tetrahydrofuran or diethyl ether
  • the resulting product is trapped with a proton donor.
  • the reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • organometallic compounds for the reaction of compounds of the formula (I-d), it is possible to use organometallic compounds, in particular
  • Alkyl lithium compounds e.g., n-butyllithium
  • EP-A-0 906 292 Alkyl lithium compounds
  • the intermediate organometallic compound is usually treated with an electrophile (e.g.
  • the process E according to the invention is usually carried out in the presence of a diluent, e.g. Tetrahydrofuran or diethyl ether, carried out at temperatures of -120 ° C to + 80 ° C.
  • a diluent e.g. Tetrahydrofuran or diethyl ether
  • the resulting product is trapped with a proton donor.
  • reaction according to the invention is preferably carried out under inert gas, in particular nitrogen or argon.
  • metals preferably zinc (cf., EP-A 0 395 175).
  • the process F according to the invention is usually carried out in the presence of a diluent, e.g. Tetrahydrofuran or organic acids, e.g. Acetic acid, carried out at temperatures of -120 ° C to + 150 ° C.
  • a diluent e.g. Tetrahydrofuran or organic acids, e.g. Acetic acid
  • Oxidizing agents in particular peroxides or peracids (eg hydrogen peroxide or meta-chloroperbenzoic acid) can be used for the reaction of I.
  • peroxides or peracids eg hydrogen peroxide or meta-chloroperbenzoic acid
  • the process G according to the invention is usually carried out in the presence of a diluent, for example dichloromethane, at temperatures of -20.degree. C. to + 100.degree.
  • a diluent for example dichloromethane
  • the heterocyclic thio-substituted alkanol derivatives of the general formula (I) according to the invention can be converted into acid addition salts or metal salt complexes.
  • physiologically acceptable acid addition salts of the compounds of general formula (I) are preferably the following acids: hydrogen halides, such as hydrochloric and hydrobromic acid, especially hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid - Re, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid and sulfonic acids such as p-toluenesulfonic acid and 1,5-naphthalene disulfonic acid.
  • hydrogen halides such as hydrochloric and hydrobromic acid, especially hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid - Re, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, sal
  • the acid addition salts of the compounds of general formula (I) can be conveniently prepared by standard salt formation techniques, e.g. by dissolving a compound of general formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid, and in a known manner, e.g. by filtration, isolated and optionally purified by washing with an inert organic solvent.
  • a suitable inert solvent e.g. Hydrochloric acid
  • metal salt complexes of the compounds of the general formula (I) preference is given to salts of metals of the IIth to IVth main groups and of the 1st and 2nd and IVth to VIIIth subgroups of the Periodic Table, where copper, zinc, Manganese, magnesium, tin, iron and nickel may be mentioned by way of example.
  • Suitable anions of the salts are those which are preferably derived from the following acids: hydrohalic acids, e.g. Hydrochloric acid and hydrobromic acid, further phosphoric acid, nitric acid and sulfuric acid.
  • the metal salt complexes of compounds of the general formula (I) can be obtained in a simple manner by conventional methods, e.g. by dissolving the metal salt in alcohol, e.g. Ethanol and adding to the compound of general formula I.
  • Metal salt complexes can be prepared in known manner, e.g. isolate by filtration and optionally purified by recrystallization.
  • the present invention further relates to a crop protection agent for controlling unwanted microorganisms, in particular unwanted fungi, comprising the active compounds according to the invention.
  • a crop protection agent for controlling unwanted microorganisms, in particular unwanted fungi, comprising the active compounds according to the invention.
  • Preference is given to fungicidal compositions which contain agriculturally useful auxiliaries, solvents, carriers, surface-active substances or extenders.
  • the invention relates to a method for controlling unwanted microorganisms, characterized in that the active compounds according to the invention are applied to the phytopathogenic fungi and / or their habitat.
  • the carrier means a natural or synthetic, organic or inorganic substance with which the active ingredients for better applicability, v. A. for planting or plant parts or seeds, mixed or connected.
  • the carrier which may be solid or liquid, is generally inert and should be useful in agriculture.
  • Suitable solid or liquid carriers are: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Minerals such as fumed silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
  • ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic Minerals such as fumed silica, alumina and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol, organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such carriers can also be used.
  • solid carriers for granules are: for example, broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Suitable liquefied gaseous diluents or carriers are those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids may be used in the formulations.
  • Other additives may be mineral and vegetable oils.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or dichloromethane, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • the agents of the invention may additionally contain other ingredients, e.g. surfactants.
  • Suitable surface-active substances are emulsifying and / or foam-forming agents, dispersants or wetting agents having ionic or nonionic properties or mixtures of these surface-active substances.
  • Examples thereof are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-sulphite liquors and methylcellulose.
  • the presence of a surfactant is necessary when one of the active ingredients and
  • Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • additional components may be included, for example, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, stabilizers, sequestering agents, complexing agents.
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90%. Active ingredient, most preferably between 10 and 70 weight percent.
  • the active compounds or compositions according to the invention can be used as such or as a function of their physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the treatment of seed, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, pesticide coated seed, suspension concentrates, suspension emulsions concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powder
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one customary extender, solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, wetting agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, antifoams, Preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • compositions according to the invention comprise not only formulations which are already ready to use and can be applied to the plant or seed by suitable equipment, but also commercial concentrates which must be diluted with water before use.
  • the active compounds according to the invention as such or in their (commercial) formulations and in the formulations prepared from these formulations in admixture with other (known) agents such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers , Safeners or semiochemicals.
  • other agents such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers , Safeners or semiochemicals.
  • the treatment according to the invention of the plants and plant parts with the active compounds or agents takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg by dipping, spraying, spraying, sprinkling, evaporation, Spraying, atomising, sprinkling, foaming, brushing, spreading, pouring, drip irrigation and, in the case of propagating material, in particular for seeds, further by dry pickling, wet dressing, slurry pickling, encrusting, single or multi-layer coating, etc. is also possible, the active ingredients according to the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself in the soil.
  • the invention further comprises a method of treating seed.
  • the invention further relates to seed which has been treated according to one of the methods described in the previous paragraph.
  • the seeds according to the invention are used in methods for the protection of seed from undesirable microorganisms.
  • a seed treated with at least one active ingredient according to the invention is used.
  • the active compounds or compositions according to the invention are also suitable for the treatment of seed.
  • Much of the damage to crop plants caused by harmful organisms is caused by the infestation of the seed during storage or after sowing and during and after germination of the plant. This phase is particularly critical because the roots and shoots of the growing plant are particularly sensitive and may cause only a small damage to the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using suitable means.
  • the present invention therefore also relates to a method of protecting seed and germinating plants from the infestation of phytopathogenic fungi by treating the seed with an agent according to the invention.
  • the invention also relates to the use of the seed treatment agents of the invention for protecting the seed and the germinating plant from phytopathogenic fungi.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against phytopathogenic fungi.
  • the active compounds or agents according to the invention can also be used in particular in the case of transgenic seed, wherein the plant growing from this seed is capable of expressing a protein which acts against pests.
  • the active compounds or agents according to the invention By treating such seeds with the active compounds or agents according to the invention, it is possible to combat pests already determined by the expression of, for example, insecticidal protein.
  • a further synergistic effect can be observed, which additionally increases the effectiveness for protection against pest infestation.
  • compositions according to the invention are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture and viticulture.
  • these are seeds of cereals (such as wheat, barley, rye, triticale, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugar beet and fodder beet), Peanut, canola, poppy, olive, coconut, cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onions and lettuce), turf and ornamental plants (see also below).
  • cereals such as wheat, barley, rye, triticale, millet and oats
  • corn cotton, soy, rice, potatoes, sunflower, bean, coffee, turnip (eg sugar beet and fodder beet)
  • Peanut canola, poppy, olive, coconut, cocoa, sugarcane, tobacco, vegetables (such as tomato, cucumber, onions and lettuce), turf and ornamental plants
  • transgenic seed As also described below, the treatment of transgenic seed with the active compounds or agents according to the invention is of particular importance.
  • the heterologous gene in transgenic seed may e.g. come from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • this heterologous gene is derived from Bacillus sp., Wherein the gene product has an activity against the European corn borer and / or Western Com Rootworm.
  • the heterologous gene is from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a condition that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seed may be used which has been harvested, cleaned and dried to a moisture content of below 15% by weight.
  • seed can also be used, which after drying, for example, treated with water and then dried again.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417, US 4,245,432, US 4,808,430, US 5,876,739, US 2003/0176428 AI, WO 2002/080675, WO 2002/028186.
  • the active compounds which can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preference is given to using alkylnaphthalene sulfonates, such as diisopropyl or diisobutylnaphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide, block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. ge. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose are preferably mentioned.
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol 2, Springer Verlag, 1970, pages 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water For the treatment of seeds of various kinds, including seeds of transgenic plants, additional synergistic effects may occur in conjunction with the substances produced by expression.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices which can usually be used for the dressing can be considered.
  • the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • a drying process follows.
  • the active compounds or compositions according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
  • Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytriomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Bactericides can be used in crop protection to control Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
  • the fungicidal compositions according to the invention can be used curatively or protectively for controlling phytopathogenic fungi.
  • the invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the active compounds or agents according to the invention, which is applied to the seed, the plant or plant parts, the fruits or the soil in which the plants grow.
  • compositions of the invention for controlling phytopathogenic fungi in crop protection comprise an effective but non-phytotoxic amount of the active compounds of the invention.
  • Effective but non-phytotoxic amount means an amount of the agent of the invention sufficient to control the fungal disease of the plant sufficient to control or completely kill and at the same time symptoms of phytotoxicity. This rate of application may generally vary over a wider range. It depends on several factors, such as the fungus to be controlled, the plant, the climatic conditions and the contents of the agents of the invention.
  • the good plant tolerance of the active ingredients in the concentrations necessary for controlling plant diseases permits treatment of aboveground plant parts, of planting and seed, and of the soil.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • the active compounds according to the invention are suitable for good plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the harvested crop. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • plants which can be treated according to the invention mention may be made of the following: cotton, flax, grapevine, fruits, vegetables, such as Rosaceae sp. (for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries), Ribeosidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp. , Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp.
  • Rosaceae sp. for example, pome fruits such as apple and pear, but also drupes such as apricots, cherries, almonds and peaches and soft fruits such as strawberries
  • Rosaceae sp. for example, pome fruits such as apple and pear
  • Rubiaceae sp. for example, coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. for example, lemons, organs and grapefruit
  • Solanaceae sp. for example tomatoes
  • Liliaceae sp. Asteraceae sp.
  • Umbelliferae sp. for example, Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. leek, onion), Papilionaceae sp.
  • Main crops such as Gramineae sp. (for example corn, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Poaceae sp. (eg sugarcane), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes and rapeseed, mustard, horseradish and cress), Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soybean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example, turnip, fodder, chard, beet); Useful plants and ornamental plants in the garden and forest; and each genetically modified species of these plants.
  • Gramineae sp. for example corn, turf, cereals
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and parts thereof are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “parts of plants” has been explained above.Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.PV plants are understood as meaning plants with new properties ("traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), eg. As plants or seeds are used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially refers to a gene that is provided or assembled outside the plant and which, when introduced into the nuclear genome, the chloroplast genome or the hypochondriacoma genome of the transformed plant, thereby imparts new or improved agronomic or other intrinsic properties.
  • RNA in A heterologous gene present in the genome is also referred to as a transgene
  • a transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event.
  • the treatment according to the invention can also lead to superadditive (“synergistic”) effects.
  • the following effects are possible expected effects: reduced application rates and / or extended spectrum of action and / or increased efficacy of the active ingredients and compositions that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or water or soil salt content , increased flowering efficiency, harvest relief, maturation acceleration, higher yields, larger fruits, greater plant height, intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the harvested products, higher sugar concentration in the Fruits, better shelf life and / or processability of the harvested products.
  • the active compounds according to the invention can also exert a strengthening effect on plants. They are therefore suitable for the mobilization of the plant defense system against attack by undesirable phytopathogenic fungi and / or microorganisms and / or viruses. This may optionally be one of the reasons for the increased effectiveness of the combinations according to the invention, for example against fungi.
  • Plant-strengthening (resistance-inducing) substances in the present context should also mean those substances or substance combinations capable of stimulating the plant defense system in such a way that the treated plants, when subsequently inoculated with undesirable phytopathogenic fungi, have a considerable degree of resistance against have these unwanted phytopathogenic fungi.
  • the substances according to the invention can therefore be employed for the protection of plants against attack by the mentioned pathogens within a certain period of time after the treatment.
  • the period of time over which a protective effect is achieved generally extends from 1 to 10 days, preferably 1 to 7 days, after the treatment of the plants with the active substances.
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material conferring on these plants particularly advantageous, useful features (whether obtained by breeding and / or biotechnology).
  • Plants and plant varieties which are also preferably treated according to the invention are resistant to one or more biotic stress factors, i. H. These plants have an improved defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are resistant to one or more abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
  • Plants and plant varieties which can also be treated according to the invention are those plants which are characterized by increased yield properties.
  • An increased yield can in these plants z. B. based on improved plant physiology, improved plant growth and improved plant development, such as water efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination and accelerated Abreife.
  • the yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, control of flowering for hybrid seed production, seedling growth, plant size, internode count and spacing, root growth, seed size, fruit size, Pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed drop, reduced pod popping and stability.
  • Other yield-related traits include seed composition such as carbohydrate content, protein content, oil content and composition, nutritional value, reduction of nontoxic compounds, improved processability, and improved shelf life.
  • Plants which can be treated according to the invention are hybrid plants which already have the properties of Heterosis or the hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors.
  • Such plants are typically produced by crossing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male crossover partner).
  • the hybrid seed is typically harvested from the male sterile plants and sold to propagators.
  • Pollen sterile plants can sometimes be produced (eg in maize) by delaving (ie mechanical removal of the male reproductive organs or the male flowers); however, it is more common for male sterility to be due to genetic determinants in the plant genome.
  • a ribonuclease such as a barnase is selectively expressed in the stamen cells in the stamens.
  • the fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants that have been tolerated to the herbicide glyphosate or its salts.
  • glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS).
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium, the CP4 gene of the bacterium Agrobacterium sp., The genes for a EPSPS from the petunia, for a EPSPS from the tomato or for a Encoding EPSPS from Eleusine.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants which select naturally occurring mutations of the above mentioned genes. Other herbicidally resistant plants are, for example, plants which have been tolerated against herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate.
  • Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme encoding a phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase have been described.
  • hydroxyphenylpyruvate dioxygenase HPPD
  • the hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogentisate.
  • Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutant HPPD enzyme.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding an HPPD-tolerant enzyme.
  • ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides.
  • ALS also known as acetohydroxy acid synthase, AHAS
  • AHAS acetohydroxy acid synthase
  • plants tolerant to imidazolinone and / or sulfonylurea can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding.
  • Plants or plant varieties obtained by plant biotechnology methods such as genetic engineering) which can also be treated according to the invention are insect-resistant transgenic plants, ie plants which have been made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such insect resistance.
  • insect-resistant transgenic plant includes any plant containing at least one transgene comprising a coding sequence encoding: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticide part thereof, such as the insecticidal crystal proteins found online at:
  • a Bacillus thuringiensis crystal protein or a part thereof which is insecticidal in the presence of a second crystal protein other than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35; or
  • an insecticidal hybrid protein comprising parts of two different insecticides of Bacillus thuringiensis crystal proteins, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
  • a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1A and VIP2A.
  • an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
  • 8) a protein according to any of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding To expand target insect species and / or due to changes induced in the coding DNA during cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102.
  • insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8.
  • an insect-resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to increase the spectrum of the corresponding target insects. or to delay the development of resistance of the insects to the plants by using various proteins that are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
  • Plants or plant varieties which can also be treated according to the invention, are tolerant of abiotic stressors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.
  • PARP poly (ADP-ribose) polymerase
  • Plants which contain a stress tolerance-enhancing transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering
  • Plants or plant varieties which can also be treated according to the invention, have a modified amount, quality and / or shelf life of the harvested product and / or altered properties of certain constituents of the harvested product on, such as:
  • Transgenic plants which synthesize a modified starch with respect to their chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the viscosity behavior, the gel strength, the starch grain size and / or starch grain morphology is altered in comparison to the synthetic starch in wild-type plant cells or plants, so that this modified starch is better suited for certain applications.
  • Transgenic plants that synthesize non-starch carbohydrate polymers or non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification.
  • Examples are plants which produce polyfructose, in particular of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,6-branched alpha-1,4-glucans and plants that produce alternan.
  • Plants or plant varieties are specially chatted with plants such as cotton plants with altered fiber.
  • Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; these include: a) plants, such as cotton plants, containing an altered form of cellulose synthase genes, b) plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids;
  • plants such as cotton plants having increased expression of sucrose phosphate synthase
  • plants such as cotton plants with increased expression of sucrose synthase
  • plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes.
  • Plants or plant varieties obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; these include:
  • plants such as oilseed rape plants, which produce oil of high oleic acid content
  • plants such as oilseed rape plants, which produce oil with a low linolenic acid content.
  • plants such as rape plants that produce oil with a low saturated fatty acid content.
  • transgenic plants which can be treated according to the invention are plants with one or more genes which code for one or more toxins, the transgenic plants which are offered under the following commercial names: YIELD GARD® (for example maize, Cotton, soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) , Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato).
  • YIELD GARD® for example maize, Cotton, soybeans
  • KnockOut® for example corn
  • BiteGard® for example maize
  • BT-Xtra® for example corn
  • StarLink® for example maize
  • Bollgard® cotton
  • Nucotn® cotton
  • Nucotn 33B® cotton
  • NatureGard® for example corn
  • Protecta® and NewLeaf® pot
  • Herbicide-tolerant crops to be mentioned are, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link® (phosphinotricin tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (sylphonylurea tolerance), for example maize.
  • Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
  • transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in the files of various national or regional authorities (see, for example, http: // /gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
  • the active compounds or compositions according to the invention can also be used in the protection of materials for the protection of industrial materials against infestation and destruction by undesired microorganisms, such as fungi and insects.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • Technical materials as used herein mean non-living materials that have been prepared for use in the art.
  • engineering materials to be protected from microbial change or destruction by the active compounds of the present invention may be adhesives, glues, paper, wallboard and board, textiles, carpets, leather, wood, paints and plastics, coolants, and other materials used by Microorganisms can be attacked or decomposed.
  • parts of production plants and buildings e.g. Cooling water circuits, cooling and heating systems and ventilation and air conditioning systems, which may be affected by the proliferation of microorganisms.
  • technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
  • the active compounds or compositions according to the invention can prevent adverse effects such as decay, deterioration, decomposition, discoloration or mold.
  • the compounds of the invention for protection against fouling of objects in particular of hulls, screens, nets, structures, quays and signal systems, which come in contact with seawater or brackish water, can be used.
  • Storage Goods are understood natural substances of plant or animal origin or their processing products, which were taken from nature and for long-term protection is desired
  • Storage goods of plant origin such as plants or plant parts, such as stems, leaves, tubers, seeds , Fruits, grains, can be protected in freshly harvested condition or after processing by (pre-) drying, wetting, crushing, grinding, pressing or roasting
  • Storage Goods also includes timber, whether unprocessed, such as timber, power poles and barriers, or in the form of finished products, such as furniture, storage goods of animal origin are, for example, skins, leather, furs and hair.
  • the active compounds according to the invention can prevent disadvantageous effects such as decay, deterioration, disintegration, discoloration or mold.
  • Blumeria species such as, for example, Blumeria graminis
  • Podosphaera species such as Podosphaera leucotricha
  • Sphaerotheca species such as Sphaerotheca fuliginea
  • Uncinula species such as Uncinula necator
  • Gymnosporangium species such as Gymnosporangium sabinae
  • Hemileia species such as Hemileia vastatrix
  • Phakopsora species such as Phakopsora pachyrhizi and Phakopsora meibomiae
  • Puccinia species such as, for example, Puccinia recondita or Puccinia triticina
  • Uromyces species such as Uromyces appendiculatus
  • Bremia species such as Bremia lactucae
  • Peronospora species such as Peronospora pisi or P. brassicae
  • Phy- tophthora species such as Phytophthora infestans
  • Plasmopara species such as, for example, Plasmopara viticola
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis
  • Pythium species such as Pythium ultimum
  • Pythium species such as Pythium ultimum
  • Phaeosphaeria species such as Phaeosphaeria nodorum
  • Pyrenophora species such as, for example, Pyrenophora teres
  • Ramularia species such as Ramularia collo-cygni
  • Rhynchosporium species such as Rhynchosporium secalis
  • Septoria species such as Septoria apii
  • Typhula species such as Typhula incarnata
  • Venturia species such as Venturia inaequalis
  • Corticium species such as Corticium granearum
  • Fusarium species such as Fusarium oxysporum
  • Gaeumannomyces species such as, for example, Gaeumannomyces graminis
  • Rhizoctonia species such as Rhizoctonia solani
  • Tapesia species such as Tapesia acuformis
  • Thielaviopsis species such as Thielaviopsis basicola
  • Ear and panicle diseases caused by e.g. Alternaria species, such as Alternaria spp .; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species such as Monographella nivalis; Septoria species, such as Septoria nodorum;
  • Alternaria species such as Alternaria spp .
  • Aspergillus species such as Aspergillus flavus
  • Cladosporium species such as Cladosporium cladosporioides
  • Claviceps species such as Claviceps purpurea
  • Fusarium species such as Fusarium culmorum
  • Gibberella species such as Gibberella
  • Sphacelotheca species such as, for example, Sphace- lotheca reiliana
  • Tilletia species such as Tilletia caries, T. controversa
  • Urocystis species such as, for example, Urocystis occulta
  • Ustilago species such as Ustilago nuda, U. nuda tritici
  • Verticilium species such as Verticilium alboatrum
  • Nectria species such as Nectria galligena
  • Botrytis species such as Botrytis cinerea
  • Diseases of plant tubers caused by e.g. Rhizoctonia species, such as Rhizoctonia solani
  • Helminthosporium species such as Helminthosporium solani
  • Xanthomonas species such as Xanthomonas campestris pv. Oryzae
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
  • Erwinia species such as Erwinia amylovora.
  • the following diseases of soybean beans can be controlled:
  • Phytophthora red (Phytophthora megaspa- ma), Brown Stem Red (Phialophora gregata), Pythium red (Pythium aphanidermatum, Pythium irregular, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), Rhizoctonia Root Red, Stem Decay, and Damping Off (Rhizoctonia solani), Sclerotinia Stem Decay (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Red (Thielaviopsis basicola).
  • microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
  • the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
  • microorganisms of the following genera Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, like Chaetomium globosum; Coniophora, like Coniophora puetana; Lentinus, like Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Escherichia, like Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus.
  • Alternaria such as Alternaria tenuis
  • Aspergillus such as Asper
  • the active compounds according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and yeasts, mold and diphasic fungi (eg against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus furnigatus, Trichophyton species such as Trichophyton mentagrophytes, Microsporon species such as Microsporon canis and audouinii.
  • Candida species such as Candida albicans, Candida glabrata
  • Epidermophyton floccosum Aspergillus species such as Aspergillus niger and Aspergillus furnigatus
  • Trichophyton species such as Trichophyton mentagrophytes
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi is by no means a limitation of
  • the application rates can be varied within a relatively wide range, depending on the mode of administration.
  • the application rate of the active compounds according to the invention is
  • Leaves from 0.1 to 10,000 g / ha, preferably from 10 to 1,000 g / ha, more preferably from 50 to 300 g / ha (when used by pouring or drop, the application rate can even be reduced, especially if inert substrates like rockwool or perlite);
  • seed treatment from 2 to 200 g per 100 kg of seed, preferably from 3 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, most preferably from 2.5 to 12, 5 g per 100 kg of seed;
  • the active compounds or compositions according to the invention can therefore be used to protect plants within a certain period of time after the treatment against attack by the mentioned pathogens.
  • the period of time within which protection is afforded generally ranges from 1 to 28 days, preferably from 1 to 14 days, more preferably from 1 to 10 days, most preferably from 1 to 7 days after treatment of the plants with the active ingredients or up to 200 days after seed treatment.
  • mycotoxins include: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxin, fumonisins, zearalenone, moniliformin, fusarin, diaceotoxyscirpenol (DAS) , Beauvericin, enniatine, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which may be caused, for example, by the following fungi: Fusarium spec., Such as Fusarium acuminatum, F.
  • the compounds according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving the plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as agents MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds according to the invention intervene in the metabolism of the plants and can therefore also be used as growth regulators.
  • Plant growth regulators can exert various types of planting effects. The effects of the substances depend essentially on the time of application, based on the stage of development of the plant and on the amounts of active substance applied to the plants or their surroundings and on the mode of administration. In any case, growth regulators should influence crop plants in a specific way.
  • Plant growth-regulating substances can be used, for example, for inhibiting the vegetative growth of the plants.
  • Such growth inhibition is of economic interest among grasses, among other things, because this can reduce the frequency of grass clippings in ornamental gardens, parks and sports facilities, on roadsides, at airports or in orchards.
  • Also of importance is the inhibition of the growth of herbaceous and woody plants on roadsides and near pipelines or overland pipelines, or more generally in areas where a high growth of the plants is undesirable.
  • growth regulators to inhibit grain elongation. This reduces or completely eliminates the risk of plant stagnation before harvesting, and growth regulators in crops can cause a stalk reinforcement that also counteracts storage, and the use of growth regulators for stalk shortening and stalk augmentation allows higher stalks to be produced Apply fertilizer to increase yield without the risk of grain storage.
  • An inhibition of vegetative growth allows for many crops a denser planting, so that multi-carrier can be achieved based on the floor area.
  • An advantage of the smaller plants obtained in this way is that the crop can be processed and harvested more easily.
  • An inhibition of the vegetative growth of the plants can also lead to increased yields that the nutrients and assimilates benefit the flower and fruit formation to a greater extent than the vegetative plant parts.
  • Growth regulators can often be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. A promotion of the vegetative At the same time, growth can also promote generative growth by producing more assimilates to produce more or more fruits.
  • Yield increases can in some cases be achieved through an intervention in the plant metabolism, without any noticeable changes in vegetative growth.
  • growth regulators a change in the composition of the plants can be achieved, which in turn can lead to an improvement in the quality of the harvested products.
  • the degradation of desirable ingredients such.
  • the production or the discharge of secondary plant ingredients can be positively influenced.
  • An example is the stimulation of latex flow in gum trees.
  • parthenocarp fruits may develop. Furthermore, the sex of the flowers can be influenced. Also, a sterility of the pollen can be produced, which has a great importance in the breeding and production of hybrid seed.
  • growth regulators Through the use of growth regulators, the branching of the plants can be controlled.
  • the development of side shoots can be promoted by breaking the apicoid dominance, which can be very desirable, especially in ornamental plant cultivation, also in connection with growth inhibition.
  • the foliage of the plants can be controlled so that a defoliation of the plants is achieved at a desired time.
  • Such defoliation plays a major role in the mechanical harvesting of cotton but is also important in other crops such as e.g. in viticulture to facilitate the harvest of interest.
  • Defoliation of the plants may also be done to reduce the transpiration of the plants before transplanting.
  • growth regulators the fruit case. On the one hand, a premature fruit drop can be prevented.
  • Growth regulators can also be used to accelerate or retard the ripeness of the crop before or after harvesting. This is of particular advantage because this can bring about an optimal adaptation to the needs of the market. In addition, growth regulators may in some cases improve the color of the fruit. In addition, with growth regulators, a temporal concentration of maturity can be achieved. This creates the conditions for that For example, in tobacco, tomatoes or coffee a complete mechanical or manual harvesting can be made in one operation.
  • the seed or bud rest of the plants can be influenced so that the plants, such as e.g. Pineapples or ornamental plants in nurseries that do not germinate, sprout or flower at a time when they are usually unwilling to do so. Delaying bud sprouting or seed germination using growth regulators may be desirable in areas prone to frost to prevent damage from late frosts.
  • growth regulators can induce plant resistance to frost, dryness or high soil salinity. This makes it possible to cultivate plants in areas that are normally unsuitable for this purpose.
  • the plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula (I) the agents according to the invention.
  • the preferred ranges given above for the active compounds or agents also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the compounds or agents specifically mentioned in the present text.
  • the invention is illustrated by the following examples. However, the invention is not limited to the examples.
  • the 'H NMR data of the following selected examples are noted in terms of' H NMR peaks. For each signal peak first the ⁇ -value in ppm and then the signal intensity in brackets and separated by a space is listed. The ⁇ value signal intensity number pairs of different signal peaks are listed separated by semicolons.
  • the peak list of an example therefore has the form: ⁇ (intensity i); 82 (intensity 2 ); ; ⁇ ; (Intensity;); ; ⁇ ⁇ (intensity ⁇
  • Example No. 17 [DMSO-D 6 ] 9.0169 (0.61); 9.0152 (0.56); 8.8972 (0.63); 7.8564 (0.70); 7.8547 (0.66); 7.6921 (0.75); 7.6907 (0.69); 7.3044 (4.73); 5.5660 (1.00); 3.7482 (0.34); 3.7171 (0.43); 3.5138 (0.42); 3.4827 (0.34); 3.3039 (108.72); 3.2072 (0.67); 3.1956 (0.69); 2.7613 (0.67); 2.7497 (0.63); 2.5089 (10.30); 2.5046 (18.32); 2,5001 (23.30); 2.4957 (15.97); 2.4914 (7.56); 1.3297 (1.60); 0.9650 (16.00); 0.8649 (0.33); -0.0002 (2.70)
  • Example No. 36 [DMSO-D 6 ] 9.0994 (1.62); 8,1727 (0.76); 8.1523 (0.81); 8.1112 (0.53); 8,1062 (0.6); 8.0945 (0.4); 8.0881 (0.59); 8.0632 (0.76); 8.0605 (0.72); 8.045 (0.87); 8.0423 (0.77); 7.9371 (1.91); 7,7753 (0.74); 7.7566 (0.93); 7.7368 (0.98); 7.7227 (0.66); 7.7175 (0.71); 7.6739 (0.7); 7.6696 (0.58); 7.6618 (0.75); 7.656 (1.25); 7.65 (0.58); 7.6422 (0.46); 7.6379 (0.5); 6.8708 (0.82); 6.614 (0.48); 6.195 (2.64); 3.7829 (0.93); 3.7489 (1.07); 3.35 (2.67); 3,308 (391.73999); 3.2848 (3.78); 2.6747 (0.38); 2.6696 (0.51); 2.6648 (0.4); 2.5394
  • Example No. 37 [DMSO-D 6 ] 8.8970 (1.75); 7.6841 (2.03); 7.6829 (1.92); 7.1994 (1.41); 7.1951 (0.56); 7.1834 (0.67); 7.1789 (2.04); 7.0866 (1.53); 7.0665 (1.10); 5.4790 (2.34); 3.6989 (0.92); 3.6678 (1.17); 3.4696 (1.11); 3.4385 (0.89); 3.3082 (9.81); 2.5098 (1.25); 2.5055 (2.35); 2.5010 (3.07); 2.4966 (2.14); 2.4923 (1.03); 2.2446 (4.81); 1.3975 (1.23); 0.9739 (0.36); 0.9546 (16.00); -0.0002 (0.50)
  • Example No. 38 [DMSO-D 6 ] 8.9063 (1.98); 7.7082 (2.06); 7.7075 (2.13); 7.5618 (1.71); 7.5580 (1.73); 7.4926 (1.69); 7.4785 (1.94); 7.2775 (1.01); 7.2738 (0.96); 7.2634 (0.89); 7.2596 (0.89); 5.6590 (0.60); 3.7927 (0.99); 3.7720 (1.15); 3,500 (1.10); 3.5292 (0.98); 3.3537 (76.61); 3.3301 (1.54); 2.5099 (4.02); 2.5069 (8.84); 2.5039 (12.22); 2.5008 (8.83); 2,498 (4.03); 0.9694 (16.00); -0.0002 (0.44)
  • Example A Blumeria graminis test (barley) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the appropriate amount. wanted concentration.
  • young plants are sprayed with the preparation of active compound in the stated application rate. After the spray coating has dried, the plants are planted with spores of Blumeria graminis f.sp. hordei pollinated. The plants are placed in a greenhouse at a temperature of about 18 ° C and a relative humidity of about 80% in order to promote the development of mildew pustules. 7 days after the inoculation the evaluation takes place. This means
  • Example B Leptosphaeria nodorum test (wheat) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young plants are sprayed with the active ingredient preparation in the stated application rate. After the spray coating has dried on, the plants are sprayed with spores with a spore suspension of Leptosphaeria nodorum.
  • the plants remain for 48 hours at 20 ° C and 100% relative humidity in an incubation cabin.
  • the plants are placed in a greenhouse at a temperature of about 22 ° C and a relative humidity of about 80%. 8 days after the inoculation the evaluation takes place. In this case, 0% means an efficiency which corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young tomato plants are sprayed with the preparation of active compound in the stated application rate.
  • the plants are inoculated with a spore suspension of Alternaria solani and then stand for 24 h at 100% relative humidity and 22 ° C.
  • the plants are at 96% relative humidity and a temperature of 20 ° C. 7 days after the inoculation the evaluation takes place.
  • 0% means an efficiency that that corresponds to that of the control, while an efficiency of 100% means that no infestation is observed.
  • Example D Sphaerotheca test (cucumber) / protective
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • young cucumber plants are sprayed with the preparation of active compound in the stated application rate.
  • the plants are inoculated with a spore suspension of Sphaerotheca fuliginea. Subsequently, the plants are placed in a greenhouse at 70% relative humidity and a temperature of 23 ° C.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)

Abstract

La présente invention concerne de nouveaux dérivés d'alcanol thiosubstitués hétérocycliques, des procédés de préparation de ces composés, des agents contenant ces composés ainsi que leur utilisation comme composés biologiquement actifs, en particulier dans la lutte contre les micro-organismes nuisibles pour la protection phytosanitaire et la protection du matériel, et comme régulateurs de croissance des plantes.
EP11721049.2A 2010-05-27 2011-05-24 Dérivés d'alcanol thiosubstitués hétérocycliques utilisés comme fongicides Withdrawn EP2576526A1 (fr)

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US35050110P 2010-06-02 2010-06-02
EP11721049.2A EP2576526A1 (fr) 2010-05-27 2011-05-24 Dérivés d'alcanol thiosubstitués hétérocycliques utilisés comme fongicides
PCT/EP2011/058437 WO2011147813A1 (fr) 2010-05-27 2011-05-24 Dérivés d'alcanol thiosubstitués hétérocycliques utilisés comme fongicides

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JP5870093B2 (ja) * 2010-05-27 2016-02-24 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 殺菌剤としてのヘテロ環式アルカノール誘導体
UA110704C2 (uk) * 2010-05-27 2016-02-10 Баєр Інтеллекчуел Проперті Гмбх Похідні гетероциклічних алканолів як фунгіциди
WO2011147811A1 (fr) 2010-05-27 2011-12-01 Bayer Cropscience Ag Dérivés d'alcanol hétérocycliques utilisés en tant que fongicides
CA2800665A1 (fr) 2010-05-27 2011-12-01 Carl Friedrich Nising Derives alcanol heterocycliques servant de fongicides
CA2856711A1 (fr) * 2011-11-25 2013-05-30 Bayer Intellectual Property Gmbh Nouveaux derives d'alcanol heterocycliques
AU2022420827A1 (en) * 2021-12-22 2024-06-13 Augustine Therapeutics Compounds and use thereof as hdac6 inhibitors

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BR112012030132A2 (pt) 2018-05-15
EA201291320A1 (ru) 2013-05-30
US20120035051A1 (en) 2012-02-09
US8445691B2 (en) 2013-05-21
CN102985414A (zh) 2013-03-20
CA2800717A1 (fr) 2011-12-01
TW201208570A (en) 2012-03-01
AR081550A1 (es) 2012-10-03
WO2011147813A1 (fr) 2011-12-01

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